Process for manufacturing vat dyestuffs of the anthanthrone series



Patented Sept. 20, 1932 WERNER, zEEwEcK, 0 EEANKEOET- N-THE- AImEEGHENHE M,eEBMANY, 'AssmN- OR TO GENERAL ANILINE WORKS INC;

DELAWARE on NEW YORK, N. Y ACORPORATION 0E PROCESS FOR mmmm "ve r 'DYESTflFFs or THE .eureerrsuewssaifls No Drawing. Application I have found that valuable vatdyestufis are obtainedby acting with a 7 agent on an aminoanthraquinonylaantl anthronyl-aniine of the general formula:

anthanthrone NH anthraquinone NH a,

- wherein n meansthe number 1 or 2, The dye stufii's thus produced'correspond to the general formula anthanthrone (-NH-anthraquinOne-NH we, e wherein n has the above signification. Th

amino anthraquinonylanth'anthronyl amines used as starting material vin my process may be obtained by condensing halogenated anthanthrones with diamino anthraquinones. The condensation is carried out by heating said compounds in naphthalene and in the presence of copper acetate and sodium acetate. When halogenated'anthanthrones are condensed with 'amino-acyl-amino-anthraquinones by heating said compounds in naphthalene and in the presence of copper acetate,-and sodium acetate, dyestufis of the same kind are produced asobtainable by my present process. But my process has the technical advantagethat it runs'v'erys-rnooth' ly and starts from cheaper anthraquinonecompounds, 7 Y In orderlto thefol lowing examples are given theparts being by weight and all temperatures in cen- =tigrade degrees. I

' stood that I am not limited to the particular conditions nor specific products l'mentioned therein, 7

V mdmplve 1 1 part of the condensation product 010- tainable from equimolecular: proportions of and 1.5-diamino-q; v v V H I ,7 v

@h' 'end sat sh P d -obtaiimd fr -1. 1' QQille -P 1i v i a l h Q eIan- .21-m n1ar -proportions' o,;1 :,5,-.

mono-bromo-anthanthrone anthraquinone (which product is a brownish black powder, tion in concentrated sulfuric acid anda bluacylating v at "180 for 2'hours, addition of 1 part of collidine.

reaction mass is .filtered and the residue is g to the-formula: further illustrate myinventlon But I wish it to be under- 7 yielding a bluish green solufiled Maya, 1929, s'e iaijno. 360,321, and in Germany May 9, 1928.

ish red hydrosulfite vat) is 'inixed with about 510 parts of 'nitro-ben' zene' and-e 8 parts of benzoyl-chloride land the mixture is stirred The cooled washed with, nitrobenzene andspirit ;and dried. The new dyestuff thus obtained correspondsto-the formula:

euthanthrone-NH- E Itrepresents dark powdersoluble in cbn r ed ulfu a i :w thye lowish olive-green tint. It'dyes'cottonfr oma reddish violet vat fast bluish grey shades.

; Examplesoluble in concentrated sulfuric acid with a; greenish-blue tint, yielding a reddish violet advantageously with the hydrosulfite vat) is treated with be'nzoylchlori de as described in the foregoing example. The newdyestufi thus obtained corresponds e do,

use

i It dissolves in; concentrated sulfuric lacid ito V a r grass green -.solut1'on andidyesicotton from a reddish violet hydrosulfite vat greenish blue shadesbfagood-fastness;

" benzoyl-chlori'de' the condensation product anisoyl-chloride diamino-anthraquinone (which condensation product is a dark powder, yielding a blackish brown solution in concentrated sulfuric acid and a turbid red hydrosulfite Vat) is treated with benzoyl-chloride as described in Example 1. The dyestuflf thus obtained cor responds to the formula:

ispractically identical to dyestuff described in. Example 4 of U. S. application Serial'No'.254,620,0f'1928. I 1

H E flat When in Example 3 benzoyl chloride is substituted by anisoyl-chloride and the process is carried out otherwise as there described, a new dyestuif is obtained which corresponds to the formula It represents a blackish blue powder soluble in concentrated sulfuric acid with a greenish; in an alkaline hydrosulfite solution with a reddish violet coloration. It dyes cotton bluish grey shades from a reddish Violet Vat.

A similar dyestufl is produced by replacing by meta-methoxy-benzoylchloride. 3- v z V v I claim 1. A process which comprises heating with on: (1-64: O.NH

an acylating agent containing a benzene nucleus an amino-anthraquinonyl-anthanthronyl-amine of the generalformula:

anthanthrone (NH anthraquinoneNH wherein a means the number 1 or 2.

2. A process which comprises heating with 'benzoyl-chloride an amino-anthraquinonylanthanthronyl a-mine of thegeneral formula:

NH-anthanthrone NH NHanthanthrone-NH diamino-anthraquinone, corresponding probably to the formula:

'anisoyl chloride the condensation product,

obtainable from commercial dibromo-'anthan throne and two'molecularproportions of 1.5-

diamino-anthraquinone, corresponding probably to the formula:

NH-anthan thtone-NH- I 6. As a new compound the, Vat dyestufi' of the probable formula: 7 V I v p v I a Ga 0 6003.

which compound represents a blackish-blue powder soluble in concentrated'sulfuric acid 'with' a greenish, in an alkaline hydrosulfite solution with a reddish-violet coloration. It dyes cotton bluish-grey shades from a reddish-violet Vat. e

In testimony whereof, I affix my signature.

WERNER ZERWEGK.

anthanthrone N H anthraquinOneeNH a,

wherein n means thenumber 1 or 2. 1 3. A process whichcomprises heating with T obtainable from commercial dibromoeanthan throne and2 molecular proportions of 1:5- 

